1-Butyl-6'-methoxy-1'-phenyl-4',6'-dihydro-1'H-spiro[piperidin-4,4'-furo[3,4-c]pyrazole] | 1021858-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-Butyl-6'-methoxy-1'-phenyl-4',6'-dihydro-1'H-spiro[piperidin-4,4'-furo[3,4-c]pyrazole]
• 英文别名: 1'-butyl-6-methoxy-1-phenylspiro[6H-furo[3,4-c]pyrazole-4,4'-piperidine]
• CAS: 1021858-30-9
• 化学式: C₂₀H₂₇N₃O₂
• 分子量: 341.453
• InChiKey: VJKLIZVDVSRNBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 6'-Methoxy-1'-phenyl-4',6'-dihydro-1'H-spiro[piperidin-4,4'-furo[3,4-c]pyrazole] 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 以59%的产率得到1-Butyl-6'-methoxy-1'-phenyl-4',6'-dihydro-1'H-spiro[piperidin-4,4'-furo[3,4-c]pyrazole]
  参考文献：
  名称：

  Synthesis and structure–affinity relationships of novel spirocyclic σ receptor ligands with furopyrazole structure

  摘要：

  The synthesis of novel spirocyclic sigma receptor ligands with high affinity is described. The cyclization of the hydroxy acetal 8, which represents a key step in the synthesis of the spirocyclic compounds 3, was supported by theoretical considerations. The affinity of the spirocyclic furopyrazoles 3a-c to the sigma receptors was determined in receptor binding studies with radioligands. The N-benzyl (3b) and N-butyl (3c) derivatives display very high sigma(1) receptor affinity (3b, K-i = 0.50 nM; 3c, K-i = 1.28 nM) and high selectivity toward the sigma(2) receptor and some other receptor systems. Calculation of crucial distances of the spirocyclic furopyrazole derivatives 3b and 3c shows good correlation with the pharmacophore model of Glennon. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.045

文献信息

• EP1982987
  申请人：——

  公开号：——

  公开（公告）日：——
• EP1982987A1
  申请人：——

  公开号：EP1982987A1

  公开（公告）日：2008-10-22
• SPIRO-PYRANO-PYRAZOLE DERIVATIVES
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP2144915B1

  公开（公告）日：2014-03-19
• [EN] SPIRO-PYRANO-PYRAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE SPIRO-PYRANO-PYRAZOLE
  申请人：ESTEVE LABOR DR

  公开号：WO2008125349A1

  公开（公告）日：2008-10-23

  [EN] The present invention relates to compounds of formula (I) having pharmacological activity towards the sigma (s) receptor, and more particularly to some spiro-pyrano-pyrazole derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis.
  [FR] Cette invention concerne des composés représentés par la formule (I) ayant une activité pharmacologique vis-à-vis du récepteur sigma (s). Plus particulièrement, cette invention concerne certains dérivés de spiro-pyrano-pyrazole, des procédés permettant de préparer de tels composés, des compositions pharmaceutiques comprenant de tels composés, ainsi que leur utilisation à des fins thérapeutiques et prophylactiques, plus particulièrement pour traiter la psychose.
• Synthesis and structure–affinity relationships of novel spirocyclic σ receptor ligands with furopyrazole structure
  作者：Torsten Schläger、Dirk Schepmann、Ernst-Ulrich Würthwein、Bernhard Wünsch

  DOI：10.1016/j.bmc.2007.12.045

  日期：2008.3.15

  The synthesis of novel spirocyclic sigma receptor ligands with high affinity is described. The cyclization of the hydroxy acetal 8, which represents a key step in the synthesis of the spirocyclic compounds 3, was supported by theoretical considerations. The affinity of the spirocyclic furopyrazoles 3a-c to the sigma receptors was determined in receptor binding studies with radioligands. The N-benzyl (3b) and N-butyl (3c) derivatives display very high sigma(1) receptor affinity (3b, K-i = 0.50 nM; 3c, K-i = 1.28 nM) and high selectivity toward the sigma(2) receptor and some other receptor systems. Calculation of crucial distances of the spirocyclic furopyrazole derivatives 3b and 3c shows good correlation with the pharmacophore model of Glennon. (C) 2007 Elsevier Ltd. All rights reserved.